scholarly journals Programmed stereoselective assembly of DNA-binding helical metallopeptides

2014 ◽  
Vol 50 (76) ◽  
pp. 11097-11100 ◽  
Author(s):  
Ilaria Gamba ◽  
Gustavo Rama ◽  
Elizabeth Ortega-Carrasco ◽  
Jean-Didier Maréchal ◽  
José Martínez-Costas ◽  
...  
Keyword(s):  
Dna Binding ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Peptide Ligands ◽  
Synthesis Methods ◽  
Cell Internalization ◽  
Dna Junctions ◽  
Great Affinity ◽  
Chiral Selectivity

We have applied solid phase peptide synthesis methods for the construction of peptide ligands that coordinate Fe(ii) ions and fold into chiral peptide helicates that show great affinity and chiral selectivity for three-way DNA junctions and promising cell-internalization properties.

scholarly journals High-affinity sequence-selective DNA binding by iridium(iii) polypyridyl organometallopeptides

2016 ◽  
Vol 52 (6) ◽  
pp. 1234-1237 ◽  
Author(s):  
Ilaria Gamba ◽  
Iria Salvadó ◽  
Rosa F. Brissos ◽  
Patrick Gamez ◽  
José Brea ◽  
...  
Keyword(s):  
Dna Binding ◽  
Cell Lines ◽  
Peptide Synthesis ◽  
Cytotoxic Effect ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Synthesis Methods ◽  
High Affinity ◽  
Dna Binding Affinity ◽  
Selective Dna Binding

We demonstrate the application of solid-phase peptide synthesis methods for assembling polynuclear Ir(iii) organometallopeptides that exhibit high DNA-binding affinity, sequence selectivity, and high cytotoxic effect towards a set of cancer cell lines.

scholarly journals The 9-Fluorenylmethoxycarbonyl (Fmoc) Group in Chemical Peptide Synthesis – Its Past, Present, and Future

2020 ◽  
Vol 73 (4) ◽  
pp. 271 ◽  
Author(s):  
Wenyi Li ◽  
Neil M. O'Brien-Simpson ◽  
Mohammed Akhter Hossain ◽  
John D. Wade
Keyword(s):  
Chemical Synthesis ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Peptide Bond ◽  
Synthesis Methods ◽  
Protecting Group ◽  
Fmoc Group ◽  
The 1960S ◽  
The Many

The chemical formation of the peptide bond has long fascinated and challenged organic chemists. It requires not only the activation of the carboxyl group of an amino acid but also the protection of the Nα-amino group. The more than a century of continuous development of ever-improved protecting group chemistry has been married to dramatic advances in the chemical synthesis of peptides that, itself, was substantially enhanced by the development of solid-phase peptide synthesis by R. B. Merrifield in the 1960s. While the latter technology has continued to undergo further refinement and improvement in both its chemistry and automation, the development of the base-labile 9-fluorenylmethoxycarbonyl (Fmoc) group and its integration into current synthesis methods is considered a major landmark in the history of the chemical synthesis of peptides. The many beneficial attributes of the Fmoc group, which have yet to be surpassed by any other Nα-protecting group, allow very rapid and highly efficient synthesis of peptides, including ones of significant size and complexity, making it an even more valuable resource for research in the post-genomic world. This review charts the development and use of this Nα-protecting group and its adaptation to address the need for more green chemical peptide synthesis processes.

The Preparation of Solid-Supported Peptide Boronic Acids Derived from 4-Borono-L-phenylalanine and their Affinity for Alizarin

2007 ◽  
Vol 60 (11) ◽  
pp. 829 ◽  
Author(s):  
Peter J. Duggan ◽  
Daniel A. Offermann
Keyword(s):  
Peptide Synthesis ◽  
Boronic Acid ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Boronic Acids ◽  
Association Constants ◽  
Synthesis Methods ◽  
Selective Binding ◽  
Binding Characteristics ◽  
Potential Use

A library of solid-supported pentapeptide diboronic acids, a ‘lysine series’ and an ‘arginine series’, has been efficiently prepared using N-Fmoc-4-pinacolatoborono-l-phenylalanine and standard solid phase peptide synthesis methods. A technique for measuring the affinity of the chromophoric diol, alizarin, to the solid-supported peptide boronic acids has been developed. Considerable variation in alizarin binding strengths, both within and between arginine and lysine series was observed, with association constants in the range 200–1100 M–1 being recorded. The selective binding characteristics of these boronic acid–peptide hybrids suggest their potential use in carbohydrate sensors and cell-specific diagnostics and therapeutics.

Automation and Control of Solid-Phase Peptide Synthesis: Methods and Technology

ChemInform ◽  
2005 ◽  
Vol 36 (46) ◽  
Author(s):  
Andrea Bagno ◽  
Silvio Bicciato ◽  
Monica Dettin ◽  
Carlo Di Bello
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Synthesis Methods ◽  
Automation And Control ◽  
And Control

scholarly journals Synthesis of Pentapeptide FWKVV (Phe-Trp-Lys-Val-Val) and Its Activity as Antioxidants

2021 ◽  
Vol 9 (1) ◽  
pp. 1-7
Author(s):  
Eka Fitri Yanti ◽  
Eviyanti Nazareth ◽  
Yuana Dwi Agustin ◽  
Mohammad Rofik Usman
Keyword(s):  
Antioxidant Activity ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Muscle Protein ◽  
Solid Phase Peptide Synthesis ◽  
Synthesis Method ◽  
Synthesis Methods ◽  
Materials Synthesis ◽  
Coupling Reagent ◽  
Ic50 Value

Antioxidant pentapeptides are pentapeptide compounds that have antioxidant activity. One of the pentapeptide compounds that have antioxidant activity is FWKVV. FWKVV is a linear pentapeptide with the amino acid sequence phenylalanine-tryptophan-lysine-valine-valine, which was first isolated to hydrolyzate the muscle protein of Miiuy croaker (Miichthysmiiuy). In addition to isolation, FWKVV compounds can be produced by the peptide synthesis method because this method requires a shorter time than the isolation method from natural materials. Synthesis methods commonly used are solution-phase peptide synthesis and solid-phase peptide synthesis (SPPS). However, the SPSS method is more efficient because it does not require purification in every process. The purpose of this study was to synthesize FWKVV compounds using the SPPS method and test their antioxidant activity. FWKVV has been synthesized using the SPPS method with HBTU/HOBt coupling reagent and Fmoc protective group. The FWKVV crud produced was 148.8 mg and had antioxidant activity against DPPH radicals with an IC50 value of 4.2 mg/mL.

A Strategy for Thioamide Incorporation During Fmoc Solid-Phase Peptide Synthesis with Robust Stereochemical Integrity

2019 ◽  
Author(s):  
luis camacho III ◽  
Bryan J. Lampkin ◽  
Brett VanVeller
Keyword(s):  
Amino Acid ◽  
Functional Groups ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Side Chains ◽  
Amino Acid Side Chains ◽  
Peptide Elongation

We describe a method to protect the sensitive stereochemistry of the thioamide—in analogy to the protection of the functional groups of amino acid side chains—in order to preserve the thioamide moiety during peptide elongation.<br>

Analytical Methods for Solid Phase Peptide Synthesis

2004 ◽  
Vol 8 (4) ◽  
pp. 291-301 ◽  
Author(s):  
Giuseppina Sabatino ◽  
Mario Chelli ◽  
Alberto Brandi ◽  
Anna Papini
Keyword(s):  
Peptide Synthesis ◽  
Analytical Methods ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis
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